Functional fragrance precursor

ABSTRACT

The present invention relates to a class of fragrance precursor compounds comprising one or more of the compounds derived from the reaction of X—OH and an aldehyde or ketone, said fragrance precursor compounds being of the formula X—O—C(R) (R*) (OR**) wherein R is a C 6-24  alkyl group, a C 6-24  aralkyl group or a C 6-24  alkaryl group; R* is H or a C 6-24  alkyl group, a C 6-24  aralkyl group or a C 6-24  alkaryl group; R** is H or X; X—O representing a moiety derived from X—OH, and wherein X—OH is a compound selected from the group consisting of surfactants, fabric softeners, softener precursor ester amines, softener precursor amido amines, hair conditioners, skin conditions, saccharides and polymers. In a second aspect it relates to a method of preparing such precusors. Further the invention relates to compositions, comprising the precursor of the invention.

TECHNICAL FIELD

[0001] The present invention relates to a class of compounds, andespecially a group of fragrance precursor compounds which are used forcreating a fragrance effect, preferably on surfaces such as fibers,skin, hair and hard surfaces. More specifically, the invention relatesto a group of fragrance precursor compounds that break down on the aboveoutlined surfaces, and as a result of this release perfume. In preferredembodiments the invention relates to certain hemiacetal and acetalcompounds. Since the perfume or fragrance is only released when thecompounds of the invention are broken down, the compounds of theinvention are capable of providing a long-lasting fragrance effect. Thatis, the compounds of the present invention provide for a sustainedrelease of fragrances.

[0002] In a further aspect, the present invention relates to a processfor preparing these precursor compounds. Fragrance precursor compoundsconsist of fragrance raw materials and functional compounds such assurfactants, polymers etc., which provide benefits such as surfaceprotection, surface conditioning, and/or surface cleaning.

[0003] In addition, the present invention relates to compositionscomprising the compounds of the invention, and to fragrance raw materialdelivery systems which provide extended fragrance benefits.

BACKGROUND OF THE INVENTION

[0004] In WO-00/72816, fragrance delivery systems are described whichcomprise pro-fragrances or pro-accords selected from at least two of thefollowing: (i) aldehyde and ketone releasing pro-fragrances, whichpro-fragrances comprise inter alia and preferably oxazolidines; (ii)β-amino pro-fragrances; and (iii) orthoester pro-accords. Thepro-fragrances described are capable of delivering fragrance rawmaterial aldehydes and ketones to especially the human skin. More indetail, said international patent application is based on the findingthat certain aldehyde fragrance raw materials, such as para-t-bucinal,cymal and lillial can be controllably released from particularheterocyclic pro-fragrances to especially the skin.

[0005] In laundry products, such as fabric softeners or detergents,generally perfume additives are present which make the said productsmore aesthetically pleasing to the consumers. The product should notonly smell pleasantly and in that way add to the purchase perception,but also impart a pleasant and preferably long lasting fragrance to thefibers or fabrics treated therewith. One of the problems the personskilled in the art is confronted with is that the amount of perfumecarryover is rather marginal; much fragrance is lost during washing anddisappears down the drain. It would be very desirable to find ways ofmore effectively delivering perfume or fragrances to fibers, fabrics andtextiles and to achieve the fragrance effect for a longer period oftime.

[0006] Colgate-Palmolive application WO 02/057400 describes a watersoluble cross-linked cationic polymer derived from the polymerisation offrom 5 to 100 mole percent of a cationic vinyl addition monomer, from 0to 95 mole percent of acrylamide, and from 70 to 300 ppm of adifunctional vinyl addition monomer cross-linking agent which enhancesfrangrance delivery from a fabric softening composition to the fabric tobe softened.

[0007] In copending Colgate-Palmolive U.S. Application Serial No.9/893,117, filed Jun. 27, 2001, there is described a fabric carecomposition comprising a cationic softening compound; a non-confinedfragrance oil; and at least one fabric or skin beneficiating ingredientsuch as a fragrance oil, contained within pressure sensitivemicrocapsules to provide enhanced delivery of such beneficiatingingredient to the fabric.

OBJECTIVES OF THE PRESENT INVENTION

[0008] The first objective of the present invention is to providealternative fragrances precursors or pro-fragrances.

[0009] It is another objective to provide a more efficient deliverysystem of fragrance or perfume to surfaces.

[0010] It is a further objective to provide functional fragranceprecursor compounds that impart long lasting fragrance benefits,especially to fiber containing materials, such as fabrics and laundry.

[0011] Moreover, it is an objective of the present invention to providea controlled or sustained release system releasing fragrance for alonger period of time.

[0012] Yet a further objective is to provide consumer productcompositions which are capable to provide sustained release offragrance.

[0013] Other objectives will become apparent from reading the followingdescription and are especially obtained for laundry products, personalcare products, hard surface care products, oral products and so on.

SUMMARY OF THE INVENTION

[0014] According to the present invention a class of chemical compounds,and especially a class of fragrance precursor compounds has been found,which form the basis of products and methods which meet at least anumber of the above-identified objectives.

[0015] More in particular, the present invention provides fragranceprecursor compounds that are capable of breakdown under ambientconditions and that are the reaction product of a reaction between ahydroxyl compound, X—OH, and an aldehyde or a ketone. More in detail,the invention relates to a fragrance precursor compound comprising oneor more of the compounds derived from the reaction of X—OH and analdehyde or ketone, said fragrance precursor compounds being of theformula X—O—C(R) (R*) (OR**) wherein R is a C₆₋₂₄ alkyl group, a C₆₋₂₄aralkyl group or a C₆₋₂₄ alkaryl group; R* is H or a C₆₋₂₄ alkyl group,a C₆₋₂₄ aralkyl group or a C₆₋₂₄ alkaryl group; R** is H or X; X—Orepresenting a moiety derived from X—OH, and wherein X—OH is a compoundselected from the group consisting of surfactants, fabric softeners,softener precursor ester amines, softener precursor amido amines, hairconditioners, skin conditions, saccharides and polymers.

[0016] In preferred embodiments X—OH is of the following structure:

[0017] wherein R₁ and R₂ are each independently, H or:

[0018] (a) C₁-C₂₂ alkylenecarboxy moiety having the formula —(CH₂)_(e)R₃wherein R₃ is —NHCOR₄; or —OCOR₄; or —NR₅COR₄; and wherein R₄ and R₅ areeach independently C₁-C₂₂ akyl or alkenyl; and e is an integer from 1 to22; or

[0019] (b) C₁-C₂₂ linear or branched alkyl; or

[0020] (c) C₁-C₂₂ linear or branched alkenyl; or

[0021] (d) C₂-C₂₂ substituted or unsubstituted alkylenoxy; or

[0022] (e) C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or

[0023] (f) C₆-C₂₂ substituted or unsubstituted aryloxy; or

[0024] (g) C₇-C₂₂ substituted or unsubstituted alkylenearyl; or

[0025] (h) C₇-C₂₂ substituted or unsubstituted alkyleneoxyary; or

[0026] (i) C₇-C₂₂ oxyalkylenearyl; or

[0027] (j) an anionic unit having the formula:

(CH₂)_(y)R₆

[0028] wherein R₆ is —SO₃M, —OSO₃M, —PO₃M, —OPO₃M, Cl or mixturesthereof, wherein M is hydrogen, or one or more salt forming cationssufficient to satisfy charge balance, or mixtures thereof;

[0029] y is an integer from 1 to about 22; or

[0030] (k) a mixture comprising at least two of (a) through (j); and

[0031] q is an integer from 0 to about 22; m is an integer from 0 toabout 22; Q is (CH₂)_(m) or (CH₂CHR₇O); R₇ is independently hydrogen,methyl, ethyl, propyl or benzyl; B is H or OH; and Y is CR₁ or N.

[0032] wherein R₁ and R₂, independently, represent C₁₂ to C₃₀ aliphatichydrocarbon groups, R₃ represents (CH₂CH₂O)_(p)H, CH₃ or H; T representsNH; n is an integer from 1 to 5; m is an integer from 1 to 5 and p is aninteger from 1 to 10.

R₁—Y—(CH₂)_(q)-(Q)_(m)-B  III.

[0033] wherein R₁ is H or:

[0034] (a) C₁-C₂₂ alkylenecarboxy moiety having the formula:—(CH₂)_(e)R₃ wherein R₃ is —NHCOR₄; or —OCOR₄; or —NR₅COR₄; and whereinR₄ and R₅ are each independently C₁-C₂₂ akyl or alkenyl; and e is aninteger from 1 to 22; or

[0035] (b) C₁-C₂₂ linear or branched alkyl; or

[0036] (c) C₁-C₂₂ linear or branched alkenyl; or

[0037] (d) C₂-C₂₂ substituted or unsubstituted alkylenoxy; or

[0038] (e) C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or

[0039] (f) C₆-C₂₂ substituted or unsubstituted aryloxy; or

[0040] (g) C₇-C₂₂ substituted or unsubstituted alkylenearyl; or

[0041] (h) C₇-C₂₂ substituted or unsubstituted alkyleneoxyaryl; or

[0042] (i) C₇-C₂₂ oxyalkylenearyl; or

[0043] (j) an anionic unit having the formula:

—(CH₂)_(y)R₆

[0044] wherein R₆ is —SO₃M, —OSO₃M, —PO₃M, —OPO₃M, Cl or mixturesthereof, wherein M is hydrogen, or one or more salt forming cationssufficient to satisfy charge balance, or mixtures thereof; y is aninteger from 1 to about 22; and

[0045] (k) a mixture comprising at least two of (a) through (j); and

[0046] q is an integer from 0 to about 22; m is an integer from 0 toabout 22; Q is (CH₂)_(m) or (CH₂CHR₇O); R₇ is independently hydrogen,methyl, ethyl, propyl or benzyl; B is H or OH; and Y is O or S.

[0047] wherein R₁ and R₂ are each independently, H or:

[0048] (a) C₁-C₂₂ alkylenecarboxy moiety having the formula:—(CH₂)_(e)R₃ wherein R₃ is —NHCOR₄; or —OCOR₄; or —NR₅COR₄; and whereinR₄ and R₅ are each independently C₁-C₂₂ akyl or alkenyl; and e is aninteger from 1 to 22; or

[0049] (b) C₁-C₂₂ linear or branched alkyl; or

[0050] (c) C₁-C₂₂ linear or branched alkenyl; or

[0051] (d) C₂-C₂₂ substituted or unsubstituted alkylenoxy; or

[0052] (e) C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or

[0053] (f) C₆-C₂₂ substituted or unsubstituted aryloxy; or

[0054] (g) C₇-C₂₂ substituted or unsubstituted alkylenearyl; or

[0055] (h) C₇-C₂₂ substituted or unsubstituted alkyleneoxyaryl; or

[0056] (i) C₇-C₂₂ oxyalkylenearyl; or

[0057] (j) an anionic unit having the formula:

—(CH₂)_(y)R₆

[0058] wherein R₆ is —SO₃M, —OSO₃M, —PO₃M, —OPO₃M, Cl or mixturesthereof, wherein M is hydrogen, or one or more salt forming cationssufficient to satisfy charge balance, or mixtures thereof; R₆ may alsobe choloride; y is an integer from 1 to about 22; and

[0059] (k) a mixture comprising at least two of (a) through 0); and

[0060] q is an integer from 0 to about 22; m is an integer from 0 toabout 22; Q is (CH₂)_(m) or (CH₂CHR₇O); R₇ is independently hydrogen,methyl, ethyl, propyl or benzyl; and mixtures thereof; B is H or OH; Yis C or N; R₈ is H or C₁-C₄ alkyl; Z⁻ is a counter anion, and preferablychloride, or methyl sulfate.

[0061] wherein R₁ and R₂ are as defined in I; R′ and R″ are eachindependently OH or R1 with the proviso that at least one of R′ and R″is OH.

[0062] In a second aspect, the present invention relates to a processfor preparing the products of the invention, comprising reacting analdehyde and or ketone and a compound X—OH. X—OH is defined as above.

[0063] In a third aspect, the present invention relates to an aqueouscomposition for fragrance delivery comprising one or more of thereaction products according to the invention. Preferably, saidcomposition of comprises a fabric softener.

BRIEF DESCRIPTION OF THE DRAWINGS

[0064] In the drawings,

[0065]FIG. 1 shows the reaction between a difatty amido amine and a C₁₀aldehyde;

[0066]FIG. 2 shows the release of fragrance from fabric treated withfabric softener containing the fragrance precursor compounds of thepresent invention after 1 and after 5 days, for a C₈, C₉ and C₁₀aldehydes by Solid Phase Micro Extraction GC/MS;

[0067]FIG. 3 shows a GC/MS spectrum of pure C₁₀ aldehyde, and thecompound released from cloth treated with a fragrance precursor compoundbased on C₁₀ aldehyde and Varisoft 510;

[0068]FIGS. 4a-4 d show the proton-NMR spectra and the ¹³C-NMR spectraof Varisoft 510 and Varisoft 510 reacted with C₁₀ aldehyde; and

[0069]FIGS. 5a-5 c show the Mass Spectrum of the reaction products ofVarisoft 510 with C₁₀ aldehyde.

DETAILED DESCRIPTION OF THE INVENTION

[0070] As mentioned herein-above, the present invention relates to thereaction product of a reaction between X—OH and an aldehyde or a ketone.In the aldehyde or ketone starting compounds of this reaction, the C₆₋₂₄alkyl moiety encompasses linear and branched alkyl groups which can haveone or more unsaturations. Such groups can be substituted withsubstituents which do not adversely affect the fragrance activity of thealdehyde or ketones. Examples of such substituents encompass F, Cl andOH.

[0071] The C₆₋₂₄ alkaryl and aralkyl moiety can also be branched andcontain substituents that do not adversely affect the fragranceproperties.

[0072] In a more preferred embodiment, X—OH preferably is of thefollowing structure:

[0073] wherein R₁ and R₂ are each independently, H or:

[0074] (a) C₁-C₂₂ alkylenecarboxy moiety having the formula —(CH₂)_(e)R₃wherein R₃ is —NHCOR₄; or —OCOR₄; or —NR₅COR₄; and wherein R₄ and R₅ areeach independently C₁-C₂₂ akyl or alkenyl; and e is an integer from 1 to22; or

[0075] (b) C₁-C₂₂ linear or branched alkyl; or

[0076] (c) C₁-C₂₂ linear or branched alkenyl; or

[0077] (d) C₂-C₂₂ substituted or unsubstituted alkylenoxy; or

[0078] (e) C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or

[0079] (f) C₆-C₂₂ substituted or unsubstituted aryloxy; or

[0080] (g) C₇-C₂₂ substituted or unsubstituted alkylenearyl; or

[0081] (h) C₇-C₂₂ substituted or unsubstituted alkyleneoxyaryl; or

[0082] (i) C₇-C₂₂ oxyalkylenearyl; or

[0083] (j) an anionic unit having the formula:

—(CH₂)_(y)R₆

[0084] wherein R₆ is —SO₃M, —OSO₃M, —PO₃M, —OPO₃M, Cl or mixturesthereof, wherein M is hydrogen, or one or more salt forming cationssufficient to satisfy charge balance, or mixtures thereof; y is aninteger from 1 to about 22; or

[0085] (k) a mixture comprising at least two of (a) through (j); and

[0086] q is an integer from 0 to about 22; m is an integer from 0 toabout 22; Q is (CH₂)_(m) or (CH₂CHR₇O); R₇ is independently hydrogen,methyl, ethyl, propyl or benzyl; B is H or OH; and Y is CR₁ or N.

[0087] The aldehydes useful in the present invention can be one or moreof, but is not limited to the following group of aldehydes:

[0088] (a) Phenylacetaldehyde; or

[0089] (b) p-methyl phenylacetaldehyde; or

[0090] (c) p-isopropyl phenylacetaldehyde; or

[0091] (d) methylnonyl acetaldehyde; or

[0092] (e) phenylpropanal; or

[0093] (f) 3-(4-t-butylphenyl)-2-methyl propanal; or

[0094] (g) 3-(4-t-butylphenyl)-propanal; or

[0095] (h) 3-(4-methoxyphenyl)-2-methylpropanal; or

[0096] (i) 3-(4-isopropylphenyl)-2-methylpropanal; or

[0097] (j) 3-(3,4-methylenedioxyphenyl)-2-methylpropanal; or

[0098] (k) 3-(4-ethylpheny)-2,2dimethylpropanal; or

[0099] (l) phenylbutanal; or

[0100] (m) 3-methyl-5-phenylpentanal; or

[0101] (n) hexanal; or

[0102] (o) trans-2-hexenal; or

[0103] (p) cis-hex-3-enal; or

[0104] (q) heptanal; or

[0105] (r) cis-4-heptenal; or

[0106] (s) 2-ethyl-2-heptenal; or

[0107] (t) 2,6-dimethylpropanal; or

[0108] (u) 2,4-heptadienal; or

[0109] (v) octanal; or

[0110] (w) 2-octenal; or

[0111] (x) 3,7-dimethyloctanal; or

[0112] (y) 3,7-dimethyl-2,6-octadien-1-al; or

[0113] (z) 3,7-dimethyl-1,6-octadien-3-al; or

[0114] (aa) 3,7-dimethyl-6-octenal; or

[0115] (bb) 3,7-dimethyl-7-hydroxyoctan-1-al; or

[0116] (cc) nonanal; or

[0117] (dd) 6-nonenal; or

[0118] (ee) 2,4-nonadienal; or

[0119] (ff) 2,6-nonadienal; or

[0120] (gg) decanal; or

[0121] (hh) 2-methyl decanal; or

[0122] (ii) 4-decenal; or

[0123] (jj) 9-decenal; or

[0124] (kk) 2,4-decadienal; or

[0125] (ll) undecanal; or

[0126] (mm) 2-methyldecanal; or

[0127] (nn) 2-methylundecanal; or

[0128] (oo) 2,6,10-trimethyl-9-undecenal; or

[0129] (pp) undec-10-enyl aldehyde; or

[0130] (qq) undec-8-enanal; or

[0131] (rr) dodecanal; or

[0132] (ss) tridecanal; or

[0133] (tt) tetradecanal; or

[0134] (uu) anisaldehyde; or

[0135] (vv) bourgenonal; or

[0136] (ww) cinnamic aldehyde; or

[0137] (xx) (α-amylcinnam-aldehyde; or

[0138] (yy) (α-hexyl cinnamaldehyde; or

[0139] (zz) methoxy cinnamaldehyde; or

[0140] (aaa) citronellal; or

[0141] (bbb)hydroxy-citronellal; or

[0142] (ccc) isocyclocitral; or

[0143] (ddd) citronellyl oxyacet-aldehyde; or

[0144] (eee) cortexaldehyde; or

[0145] (fff) cumminic aldehyde; or

[0146] (ggg) cyclamem aldehyde; or

[0147] (hhh) florhydral; or

[0148] (iii) heliotropin; or

[0149] (jjj) hydrotropic aldehyde; or

[0150] (kkk) lilial; or

[0151] (lll) vanillin; or

[0152] (mmm) ethyl vanillin; or

[0153] (nnn) benzaldehyde; or

[0154] (ooo) p-methyl benzaldehyde; or

[0155] (ppp) 3,4-dimethoxybenzaldehyde; or

[0156] (qqq) 3-and4-(4-hydroxy-4-methyl-pentyl)-3-cyclohexene-1-caroxaldehyde; or

[0157] (rrr) 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde; or

[0158] (sss) 1-methyl-3-4-methylpentyl-3-cyclohexencarboxaldehyde; and

[0159] (ttt) p-methylphenoxyacetaldehyde

[0160] When an aldehyde is used the precursor of the invention is anacetal or hemiacetal.

[0161] The ketones useful in the present invention can be one or moreof, but is not limited to the group of following ketones:

[0162] (a) alpha-damascone; or

[0163] (b) beta-damascone; or

[0164] (c) delta-damascone; or

[0165] (d) beta-damascenone; or

[0166] (e) muscone; or

[0167] (f) 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone; or

[0168] (g) cashmeran; or

[0169] (h) cis-jasmone; or

[0170] (i) dihydrojasmone; or

[0171] (j) alpha-ionone; or

[0172] (k) beta-ionone; or

[0173] (l) dihydro-beta-ionone; or

[0174] (m) gamma-methyl ionone; or

[0175] (n) alpha-iso-methyl ionone; or

[0176] (o) 4-(3,4-methylenedioxyphenyl)butan-2-one; or

[0177] (p) 4-(4-ydroxyphenyl)butan-2-one; or

[0178] (q) methyl beta-naphthyl ketone; or

[0179] (r) methyl cedryl ketone; or

[0180] (s) 6-acetyl-1,1,2,4,4,7-hexamethyltetralin (tonalid); or

[0181] (t) 1-carvone; or

[0182] (u) 5-cyclohexadecen-1-one; or

[0183] (v) acetophenone; or

[0184] (w) decatone; or

[0185] (x) 2-[2-(4-methyl-3-cyclohexenyl-1-yl)propyl]cyclopentan-2-one;or

[0186] (y) 2-sec-butylcyclohexanone; or

[0187] (z) beta-dihydro ionone; or

[0188] (aa) allyl ionone; or

[0189] (bb) alpha-irone; or

[0190] (cc) alpha-cetone; or

[0191] (dd) alpha-irisone; or

[0192] (ee) acetanisole; or

[0193] (ff) geranyl acetone; or

[0194] (gg) 1-(2-methl-5-isopropyl-2-cyclohexenyl)-1-propanone; or

[0195] (hh) acetyl diisoamylene; or

[0196] (ii) methyl cyclocitrone; or

[0197] (ii) 4-t-pentyl cyclohexanone; or

[0198] (kk) p-t-butylcclohexanone; or

[0199] (ll) o-t-butylcyclohexanone; or

[0200] (mm) ethyl amyl ketone; or

[0201] (nn) ethyl pentyl ketone; or

[0202] (oo) menthone; or

[0203] (pp) methyl-7,3-dihydro-2H-1,5-benzodioxepine-3-one; or

[0204] (qq) fenchone; or

[0205] (rr) methyl naphthyl ketone; or

[0206] (ss) propyl naphthy ketone; and

[0207] (tt) methyl hydroxynaphthyl ketone

[0208] The fragrance precursor compounds of the invention were found toact as source for long lasting fragrance benefits, especially whenapplied to on surfaces such as fibers, skin, hair and hard surfaces,especially to fabrics and laundry. More specifically, the inventionrelates to fragrance precursor compounds that break down on surfacessuch as fibers, skin, hair and hard surfaces, especially to fabrics andlaundry, and as a result of this, release perfume.

[0209] Since the perfume or fragrance is only released when thecompounds of the invention are broken down, the compounds of theinvention are capable of providing a long-lasting fragrance effect. Thatis, the compounds of the present invention provide for a sustainedrelease of fragrances.

[0210] In accordance with the present invention there is a balancebetween the degree of breakdown of the fragrance precursor compounds toform the fragrance and the intensity of the fragrance. The intensity ofthe fragrance is substantially based on the fragrance formed.

[0211] To guarantee also the release of fragrance after a few days, suchas after 5 and preferably after 7 days, the fragrance must be releasedby a controlled breakdown of the fragrance precursor compounds of theinvention. That is, the equilibrium between the fragrance precursorcompounds and the components including the fragrance must preferably besuch that sufficient fragrance is released during a number of days. Thisequilibrium depends on the type of aldehyde and or ketone and the natureof compound X—OH.

[0212] In another embodiment of the present invention, the fragranceprecursor compound of the invention is derived from a compound X—OH,selected from the group consisting of polyalkylene glycol, polyalkyleneglycol ester and polysaccharide. Preferably, the polyalkylene glycol orthe ester thereof are based on polyethylene glycol, polypropylene glycoland poly(ethylene/propylene) glycol.

[0213] The fragrance precursor compounds of the present invention areespecially aimed to be incorporated in compositions to treat surfacessuch as fibers, skin, hair and hard surfaces, especially to fabrics andlaundry. From that perspective, it would be highly desirable to haveavailable compounds which not only are compatible with compositions usedto treat such materials, but additionally would have properties usefulin such compositions. In this respect, in specifically preferredembodiments, the present invention relates to fragrance precursorcompounds of the type described herein-above, wherein X—OH is asurfactant described herein-above as I. The preferred structure is ofthe formula (R₁—(CH₂)_(z))—N—(CH₂)_(y)—OH, wherein R₁, independently, isselected from the group consisting of a fatty amido amine moiety of theformula AlkC(O)NH—, a moiety having the formula AlkC(O)O, a moietyhaving the formula Alk—O—, wherein Alk is a linear or branched C₂-C₂₄alkyl or alkylene group, optionally substituted with one or morehydroxyl groups, nitro groups, amine groups, and/or halogen atoms, orrepresents a CHOH—R group. z and y, independently, are integers having avalue between 0 and 10, preferably between 0 and 5, more preferablybetween 1 and 3; x represents 2 or 3.

[0214] These fragrance precursor compounds are for instance based onfatty or di fatty amido amines, which in themselves have fabricsoftening properties. Examples of such fatty amido amines are forinstance the fabric softeners sold under the trade name Varisoft, suchas Varisoft 510 (ex Goldschmidt, Germany) as mentioned in U.S. Pat. No.5,501,806. As will follow from the examples herein-below the reactionproduct between a di fatty amido amine (Varisoft 510) and C₈₋₁₂aldehydes give pro-fragrances that give continuous release of thealdehydes until after more than 1 week.

[0215] The fragrance precursor compounds of the invention can beobtained by reacting an aldehyde and or ketone fragrance and a compoundX—OH; X—OH is selected from the group consisting of surfactants, fabricsofteners, softener precursor ester amines or amido amines, hair andskin conditioners and polymers. This forms a further aspect of thepresent invention.

[0216] In fact, the formation of a acetal, hemiacetal, and or a ketalinvolves a compound comprising at least one nucleophilic free —OH groupand an aldehyde and or ketone. This reaction is known per se.Preferably, this reaction is carried out in an aqueous solution in thepresence of an acid or a catalyst.

[0217] In FIG. 1, the reaction between an amido amine and a C₁₀ aldehydeis shown as an example. An example of the amido amine starting compoundis Varisoft 510. The products obtained from this reaction can verysuitably be incorporated in a product formula such as a rinse cyclefabric softener, and from said formula be delivered to a surface to givea long lasting fragrance.

[0218] Dependent on the number of free hydroxyl groups, one or morealdehyde and or ketone molecules can be coupled to the XOH molecule.This makes that the capacity of fragrance to be released can becontrolled to some degree.

[0219] In yet a further aspect, the present invention relates to anaqueous composition for fragrance delivery comprising one or morefragrance precursor compounds according to the invention. Preferablesaid aqueous composition is a fabric softener composition and especiallya rinse cycle fabric softener composition.

[0220] Good results are obtained when incorporating between 0.001-10 wt.% of fragrance precursor of the invention, drawn to the total weight ofthe composition, in the aqueous composition. Preferably between 0.01 and35 wt. % and more preferably between 2 and 15 wt. % of any fabricsoftening active ingredient is present. A preferred cationic softener isan esterquat softener having the following structural formula:

[0221] wherein R4 represents an aliphatic hydrocarbon group having from8 to 22 carbon atoms, R2 and R3 represent (CH₂)_(s)—R₅ where R₅represents an alkoxy carbonyl group containing from 8 to 22 carbonatoms, benzyl, phenyl, (C1-C4)-alkyl substituted phenyl, OH or H; q, s,and t, each independently, represent an integer from 1 to 3; and X⁻ is asoftener compatible anion.

[0222] The invention will be described in more detail in the followingexamples, which do not limit the invention, but merely illustrate theinvention. Unless otherwise indicated, all percentages are by weightdrawn to the weight of the final composition.

EXAMPLE 1

[0223] Fragrance precursors can be formed by preferable but not limitedto combining Varisoft 510 (3.0 g) with decyl aldehyde (1.8 ml), water(0.2 ml) and p-toluenesulfonic acid monohydrate (20 mg). The reactionwas then heated in a 60° C. oil bath with stirring overnight open to theair. The reaction was then cooled to room temperature and solidifiedupon standing. In FIG. 4, the proton- and ¹³C-NMR spectra are given ofVarisoft 510 and of Varisoft 510 reacted with C₁₀ aldehyde. FIG. 5 showsthe mass spectrum of the reaction products.

[0224] Fragrance precursors can also be formed by preferable but notlimited to the above reaction without the addition of water.

EXAMPLE 2

[0225] Fabric softener compositions are prepared comprising 5 wt. %esterquat having the following structural formula:

[0226] wherein R4 represents an aliphatic hydrocarbon group having from8 to 22 carbon atoms, R2 and R3 represent (CH₂)_(s)—R₅ where R₅represents an alkoxy carbonyl group containing from 8 to 22 carbonatoms, benzyl, phenyl, (C1-C4)-alkyl substituted phenyl, OH or H; q, s,and t, each independently, represent an interger from 1 to 3; and X— isa softener compatible anion. 1 wt. % of the amido amine fragranceprecursor compounds prepared; and 94 wt. % water. Fabric was treatedwith the fabric softener composition prepared, and the release offragrance was measured after 1 day and after 5 days by solid phase microextraction (SPME) coupled with GC/MS. For C₁₀ aldehydes the amount offragrance released on day 1 and on day 5 is about the same. Showing thedesired sustained release of fragrance from the fabric surface.

What is claimed is:
 1. A fragrance precursor compound comprising one ormore of the compounds derived from the reaction of X—OH and an aldehydeor ketone, said fragrance precursor compounds being of the formulaX—O—C(R) (R*) (OR**) wherein R is a C₆₋₂₄ alkyl group, a C₆₋₂₄ aralkylgroup or a C₆₋₂₄ alkaryl group; R* is H or a C₆₋₂₄ alkyl group, a C₆₋₂₄aralkyl group or a C₆₋₂₄ alkaryl group; R** is H or X; X—O representinga moiety derived from X—OH, and wherein X—OH is a compound selected fromthe group consisting of surfactants, fabric softeners, softenerprecursor ester amines, softener precursor amido amines, hairconditioners, skin conditions, saccharides and polymers.
 2. Thefragrance precursor of claim 1, wherein X—OH is of the followingstructure:

wherein R₁ and R₂ are each independently, H or: (a) C₁-C₂₂alkylenecarboxy moiety having the formula —(CH₂)_(e)R₃ wherein R₃ is—NHCOR₄; or —OCOR₄; or —NR₅COR₄; and wherein R₄ and R₅ are eachindependently C₁-C₂₂ akyl or alkenyl; and e is an integer from 1 to 22;or (b) C₁-C₂₂ linear or branched alkyl; or (c) C₁-C₂₂ linear or branchedalkenyl; or (d) C₂-C₂₂ substituted or unsubstituted alkylenoxy; or (e)C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or (f) C₆-C₂₂substituted or unsubstituted aryloxy; or (g) C₇-C₂₂ substituted orunsubstituted alkylenearyl; or (h) C₇-C₂₂ substituted or unsubstitutedalkyleneoxyaryl; or (i) C₇-C₂₂ oxyalkylenearyl; or (j) an anionic unithaving the formula: —(CH₂)_(y)R6 wherein R₆ is —SO₃M, —OSO₃M, —PO₃M,—OPO₃M, Cl or mixtures thereof, wherein M is hydrogen, or one or moresalt forming cations sufficient to satisfy charge balance, or mixturesthereof; y is an integer from 1 to about 22; or (k) a mixture comprisingat least two of (a) through (j); and q is an integer from 0 to about 22;m is an integer from 0 to about 22; Q is (CH₂)_(m) or (CH₂CHR₇O); R₇ isindependently hydrogen, methyl, ethyl, propyl or benzyl; B is H or OH;and Y is CR₁ or N.
 3. The fragrance precursor of claim 1, wherein X—OHis of the following structure:

wherein R₁ and R₂, independently, represent C₁₂ to C₃₀ aliphatichydrocarbon groups, R₃ represents (CH₂CH₂O)_(p)H, CH₃ or H; T representsNH; n is an integer from 1 to 5; m is an integer from 1 to 5 and p is aninteger from 1 to
 10. 4. The fragrance precursor of claim 3, wherein R₃represents (CH₂CH₂O)_(p)H; n is 2; m is 2; and p has a value from 1.5 to10.
 5. The fragrance precursor of claim 1, wherein X—OH is of thefollowing structure: R₁—Y—(CH₂)_(q)—(Q)_(m)—B wherein R₁ is H or: (a)C₁-C₂₂ alkylenecarboxy moiety having the formula: —(CH₂)_(e)R₃ whereinR₃ is —NHCOR₄; or —OCOR₄; or —NR₅COR₄; and wherein R₄ and R₅ are eachindependently C₁-C₂₂ akyl or alkenyl; and e is an integer from 1 to 22;or (b) C₁-C₂₂ linear or branched alkyl; or (c) C₁-C₂₂ linear or branchedalkenyl; or (d) C₂-C₂₂ substituted or unsubstituted alkylenoxy; or (e)C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or (f) C₆-C₂₂substituted or unsubstituted aryloxy; or (g) C₇-C₂₂ substituted orunsubstituted alkylenearyl; or (h) C₇-C₂₂ substituted or unsubstitutedalkyleneoxyaryl; or (i) C₇-C₂₂ oxyalkylenearyl; or (j) an anionic unithaving the formula: —(CH₂)_(y)R₆ wherein R₆ is —SO₃M, —OSO₃M, —PO₃M,—OPO₃M, Cl or mixtures thereof, wherein M is hydrogen, or one or moresalt forming cations sufficient to satisfy charge balance, or mixturesthereof; y is an integer from 1 to about 22; and (k) a mixturecomprising at least two of (a) through (j); and q is an integer from 0to about 22; m is an integer from 0 to about 22; Q is (CH₂)_(m) or(CH₂CHR₇O); R₇ is independently hydrogen, methyl, ethyl, propyl orbenzyl; B is H or OH; and Y is O or S.
 6. The fragrance precursor ofclaim 1, wherein X—OH is of the following structure:

wherein R₁ and R₂ are each independently, H or: (a) C₁-C₂₂alkylenecarboxy moiety having the formula: —(CH₂)_(e)R₃ wherein R₃ is—NHCOR₄; or OCOR₄; or —NR₅COR₄; and wherein R₄ and R₅ are eachindependently C₁-C₂₂ akyl or alkenyl; and e is an integer from 1 to 22;or (b) C₁-C₂₂ linear or branched alkyl; or (c) C₁-C₂₂ linear or branchedalkenyl; or (d) C₂-C₂₂ substituted or unsubstituted alkylenoxy; or (e)C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or (f) C₆-C₂₂substituted or unsubstituted aryloxy; or (g) C₇-C₂₂ substituted orunsubstituted alkylenearyl; or (h) C₇-C₂₂ substituted or unsubstitutedalkyleneoxyaryl; or (i) C₇-C₂₂ oxyalkylenearyl; or (j) an anionic unithaving the formula: —(CH₂)_(y)R₆ wherein R₆ is —SO₃M, —OSO₃M, —PO₃M,—OPO₃M, Cl or mixtures thereof, wherein M is hydrogen, or one or moresalt forming cations sufficient to satisfy charge balance, or mixturesthereof; R₆ may also be choloride; y is an integer from 1 to about 22;and (k) a mixture comprising at least two of (a) through (j); and q isan integer from 0 to about 22; m is an integer from 0 to about 22; Q is(CH₂)_(m) or (CH₂CHR₇O); R₇ is independently hydrogen, methyl, ethyl,propyl or benzyl; and mixtures thereof; B is H or OH; Y is C or N; R8 isH or C₁-C₄ alkyl; Z is a counter anion, and preferably chloride, ormethyl sulfate.
 7. The fragrance precursor of claim 1, wherein X—OH is apolyol.
 8. The fragrance precursor of claim 1, wherein X—OH is of thefollowing structure:

wherein R₁ and R₂ are as defined in claim 1; R′ and R″ are eachindependently OH or R₁ with the proviso that at least one of R′ and R″is OH.
 9. The fragrance precursor of claim 1, wherein the moietyC(R)(OR**)(R*) is derived from one or more of the following aldehydes:(a) Phenylacetaldehyde; or (b) p-methyl phenylacetaldehyde; or (c)p-isopropyl phenylacetaldehyde; or (d) methylnonyl acetaldehyde; or (e)phenylpropanal; or (f) 3-(4-t-butylphenyl)-2-methyl propanal; or (g)3-(4-t-butylphenyl)-propanal; or (h)3-(4-methoxyphenyl)-2-methylpropanal; or (i)3-(4-isopropylphenyl)-2-methylpropanal; or (j)3-(3,4-methylenedioxyphenyl)-2-methylpropanal; or (k)3-(4-ethylpheny)-2,2dimethylpropanal; or (l) phenylbutanal; or (m)3-methyl-5-phenylpentanal; or (n) hexanal; or (o) trans-2-hexenal; or(p) cis-hex-3-enal; or (q) heptanal; or (r) cis-4-heptenal; or (s)2-ethyl-2-heptenal; or (t) 2,6-dimethylpropanal; or (u) 2,4-heptadienal;or (v) octanal; or (w) 2-octenal; or (x) 3,7-dimethyloctanal; or (y)3,7-dimethyl-2,6-octadien-1-al; or (z) 3,7-dimethyl-1,6-octadien-3-al;or (aa) 3,7-dimethyl-6-octenal; or (bb)3,7-dimethyl-7-hydroxyoctan-1-al; or (cc) nonanal; or (dd) 6-nonenal; or(ee) 2,4-nonadienal; or (ff) 2,6-nonadienal; or (gg) decanal; or (hh)2-methyl decanal; or (ii) 4-decenal; or (jj) 9-decenal; or (kk)2,4-decadienal; or (ll) undecanal; or (mm) 2-methyldecanal; or (nn)2-methylundecanal; or (oo) 2,6,10-trimethyl-9-undecenal; or (pp)undec-10-enyl aldehyde; or (qq) undec-8-enanal; or (rr) dodecanal; or(ss) tridecanal; or (tt) tetradecanal; or (uu) anisaldehyde; or (vv)bourgenonal; or (ww) cinnamic aldehyde; or (xx) α-amylcinnam-aldehyde;or (yy) α-hexyl cinnamaldehyde; or (zz) methoxy cinnamaldehyde; or (aaa)citronellal; or (bbb) hydroxy-citronellal; or (ccc) isocyclocitral; or(ddd) citronellyl oxyacet-aldehyde; or (eee) cortexaldehyde; or (fff)cumminic aldehyde; or (ggg) cyclamem aldehyde; or (hhh) florhydral; or(iii) heliotropin; or (jjj) hydrotropic aldehyde; or (kkk) lilial; or(lll) vanillin; or (mmm) ethyl vanillin; or (nnn) benzaldehyde; or (ooo)p-methyl benzaldehyde; or (ppp) 3,4-dimethoxybenzaldehyde; or (qqq)3-and 4-(4-hydroxy-4-methyl-pentyl)-3-cyclohexene-1-caroxaldehyde; or(rrr) 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde; or (sss)1-methyl-3-4-methylpentyl-3-cyclohexencarboxaldehyde; and (ttt)p-methylphenoxyacetaldehyde.
 10. The fragrance precursor of claim 1,wherein the moiety—CHOR*-R is derived from one or more of the followingketones: (a) alpha-damascone; or (b) beta-damascone; or (c)delta-damascone; or (d) beta-damascenone; or (e) muscone; or (f)6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone; or (9) cashmeran; or(h) cis-jasmone; or (i) dihydrojasmone; or (j) alpha-ionone; or (k)beta-ionone; or (l) dihydro-beta-ionone; or (m) gamma-methyl ionone; or(n) alpha-iso-methyl ionone; or (o)4-(3,4-methylenedioxyphenyl)butan-2-one; or (p)4-(4-ydroxyphenyl)butan-2-one; or (q) methyl beta-naphthyl ketone; or(r) methyl cedryl ketone; or (s) 6-acetyl-1,1,2,4,4,7-hexamethyltetralin(tonalid); or (t) 1-carvone; or (u) 5-cyclohexadecen-1-one; or (v)acetophenone; or (w) decatone; or (x)2-[2-(4-methyl-3-cyclohexenyl-1-yl)propyl]cyclopentan-2-one; or (y)2-sec-butylcyclohexanone; or (z) beta-dihydro ionone; or (aa) allylionone; or (bb) alpha-irone; or (cc) alpha-cetone; or (dd)alpha-irisone; or (ee) acetanisole; or (ff) geranyl acetone; or (gg)1-(2-methl-5-isopropyl-2-cyclohexenyl)-1-propanone; or (hh) acetyldiisoamylene; or (ii) methyl cyclocitrone; or (jj) 4-t-pentylcyclohexanone; or (kk) p-t-butylcclohexanone; or (ll)o-t-butylcyclohexanone; or (mm) ethyl amyl ketone; or (nn) ethyl pentylketone; or (oo) menthone; or (pp)methyl-7,3-dihydro-2H-1,5-benzodioxepine-3-one; or (qq) fenchone; or(rr) methyl naphthyl ketone; or (ss) propyl naphthy ketone; and (tt)methyl hydroxynaphthyl ketone.
 11. A fragrance precursor compounddelivery system comprising: (a) at least about 0.001% by weight, of afragrance precursor conjugate, comprising: (i) a fragrance precursorcompound as in claim 1 capable of releasing a fragrance raw material; or(ii) a fragrance raw material; and (b) the balance carriers and adjunctingredients.
 12. A laundry detergent comprising: (a) at least about0.001% by weight, of a fragrance precursor conjugate, comprising: (i) afragrance precursor compound as in claim 1 capable of releasing afragrance raw material; or (ii) a fragrance raw material; and (b)effective amount of a detersive surfactant; and (c) the balance carriersand adjunct ingredients.
 13. A fabric softener or fabric softening dryersheet comprising: (a) at least about 0.001% by weight, of a fragranceprecursor conjugate, comprising: (i) a fragrance precursor compound asin claim 1 capable of releasing a fragrance raw material; or (ii) afragrance raw material; and (b) effective amount of a fabric softeningcompound; and (c) the balance carriers and adjunct ingredients.
 14. Aperfume or fine fragrance comprising; (a) at least about 0.001% byweight, of a fragrance precursor conjugate, comprising: (i) a fragranceprecursor compound as in claim 1 capable of releasing a fragrance rawmaterial; or (ii) a fragrance raw material; and (c) at least about 0.01%to about 99% by weight, of an admixture of fragrance raw materials; and(d) the balance carriers and adjunct ingredients.
 15. A personal careproduct, or oral care product or hard surface care product comprising;(a) from about 0.001% by weight, of a fragrance precursor conjugate,comprising: (i) a fragrance precursor compound as in claim 1 capable ofreleasing a fragrance raw material; or (ii) a fragrance raw material;and (b) from about 0.1% by weight, of a surfactant, or emollient orabrasive or anti-bacterial agent suitable for use in personal care ororal care or hard surface care products; and (c) the balance carriersand adjunct ingredients.
 16. A composition according to one of claims11, 12, 13, 14 or 15 wherein said carriers and adjunct ingredients areselected from the group consisting of builders, optical brighteners,bleaches, bleach boosters, bleach catalysts, bleach activators, soilrelease polymers, dye transfer agents, dispersents, enzymes, sudssuppressers, dyes, perfumes, colorants, filler salts, hydrotropes,photoactivators, fluorescers, fabric conditioners, hydrolyzablesurfactants, preservatives, anti-oxidants, chelants, stabilizers,anti-shrinkage agents, anti-wrinkle agents, germicides, fungicides, anticorrosion agents, and mixtures thereof.
 17. A method of preparing afragrance precursor compound of the formula X—O—C(R)(R*)(OR**) wherein Ris a C₆₋₂₄ alkyl group, a C₆₋₂₄ aralkyl group or a C₆₋₂₄ alkaryl group;R* is H or a C₆₋₂₄ alkyl group, a C₆₋₂₄ aralkyl group or a C₆₋₂₄ alkarylgroup; R** is H or X; X—O representing a moiety derived from X—OH andwherein X—OH is a compound selected from the group consisting ofsurfactants, fabric softeners, softener precursor ester amines, softenerprecursor amido amines, hair conditioners, skin conditions, saccharidesand polymers, said method comprising reacting an aldehyde or ketonefragrance of the formula R—C(O)R* and a compound represented by X—OH.18. The method of claim 17, wherein the reaction is acid catalyzed.